


Secrets

by SoftIceCream



Category: The Office (US)
Genre: Feminization, Gender Confusion, Jim's an attention whore and knows it, Light Dom/sub, M/M, Porn With Plot, Smut, Why Did I Write This?
Language: English
Status: Completed
Published: 2020-08-26
Updated: 2020-08-26
Packaged: 2021-03-07 01:55:13
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 9,394
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26119132
Author URL: https://archiveofourown.org/users/SoftIceCream/pseuds/SoftIceCream
Summary: Everyone has secrets. Maybe Jim shouldn’t have advertised his on Instagram.
Relationships: Jim Halpert/Michael Scott
Comments: 17
Kudos: 45





	Secrets

**Author's Note:**

> This fic has not been beta read. Let me know if you see any mistakes.

It was a fairly typical day at Dunder Mifflin. There was work to be done, calls to be made, annoying coworkers to annoy back. The same ole same ole. Jim quickly processed all of his work, finishing before lunchtime. He planned on making his final rounds after lunch before spending the last two hours or so plotting his after-work activities. Having a plan made his life so much easier and allowed him to get all the equipment he needed. It made cleanup much easier too.

While on his last sales call of the day, Jim was tapped on the shoulder by Michael. Fighting the urge to roll his eyes at the man, Jim politely smiled and hurriedly ended his phone call. He followed Michael into his office and shut the door behind him.

“Jimborooni! How have you been,” Michael asked jovially.

“I’ve been better,” Jim answered. “Is there something you needed, or…?”

“Yeah! I was thinking you and me can get dinner today! Two bros hanging out! Or like a date! You’d like that, wouldn’t you?”

Jim ignored Michael’s attempted jab at his sexuality. Michael (and Dwight, and Roy, and on occasion, Kevin) poked fun at him for not being as “macho” as they were. Jim never let it bother him; he heard it all while growing up and his lowlife coworkers weren’t going to get the best of him. “I can’t today, I have plans after work.”

“No you don’t,” Michael said in his same, cheerful voice.

Jim frowned at that. “Michael, I have stuff to do. I can’t get dinner with you.”

Michael gestured for Jim to come behind his desk. Nervous, Jim did so. He leaned over Michael’s chair to see what was on his boss’s computer screen.

Jim’s jaw dropped. 

In his browser Michael had an Instagram page pulled up. It was of a man who was _very_ good at makeup. Every picture was of a different, high-concept look that the man pulled off using makeup and sometimes prosthetics and body paint. In some photos, the man did half-drag with different wigs. In others, he did full-drag. He had over two-hundred thousand followers but no identifiable information. Part of the appeal seemed to be that the man was an enigma. A beautifully done-up enigma.

It was Jim’s “secret” Instagram page.

Jim collected his jaw and trained his face into something more neutral before Michael caught on to him. “Interesting. Why are you showing me this?”

Michael exaggeratedly rolled his eyes. “It’s you, Jim.”

“Ahh. Nope, I don’t think that’s me.”

“It’s definitely you. He looks just like you but with makeup. See,” Michael pointed at his monitor. “When you don’t contour your nose then it looks the way it usually does. And if you don’t wear contacts then your eyes are the same. No wig? Same hair. I’ve cracked the case!”

Jim wanted to know why Michael knew what a “contour” was. “It’s not me. I don’t know what else to tell you, Michael.”

“Then you won’t have any problem with me showing this account to the rest of the office? I really admire his makeup skills. I’m sure everyone else will too!”

Let it be known that Jim was not afraid of Michael. Michael could threaten him all he wanted. But Jim didn’t necessarily want Pam or Dwight knowing about his hobby. Jim wasn’t out to anyone at work and couldn’t gauge how Pam would take it if she knew he was a) gay and b) liked doing makeup. He could take the men at work ostracizing him over this but Jim would be absolutely gutted if Pam did the same. And Dwight...Dwight was another can of worms. He seemed like the type to do hate crimes. Jim didn’t want any smoke.

“What do you want, Michael,” Jim whispered into his ear.

“Us, dinner.”

“Is that it?” Jim could do dinner. He’d want to kill himself before, during, and after, but he could do it.

“I want to watch too,” Michael said with a waggle of his eyebrow. “Can I watch?”

Jim didn’t understand. Watch what? If Michael was propositioning him for sex then Jim could bypass this whole issue and report Michael to HR. Not that Toby would do anything. “What?”

“I want to watch you do your makeup. See the transformation in person. _See the magic_!”

Jim frowned. This was creepy, even for Michael. However, Jim didn’t have much of a choice. “Fine. Do you want to come to my place this weekend…?”

“It has to be tonight,” Michael said giddily. 

“Fine. Then dinner has to be quick. It takes a few hours for me to do...you know…”

Michael nodded eagerly and Jim took that as a sign to leave.

* * *

Dinner was a quick affair. They ate Chipotle since Michael thought it was the greatest thing ever. He made a big show of buying Jim’s burrito bowl before pulling out his chair and picking Jim’s favorite soda from the dispenser. The employees gave them strange looks, with one of them asking if Jim was Michael’s respite caregiver. Jim would say he was embarrassed but this was normal Michael antics.

“How do you get into the makeup mood,” Michael asked, wide-eyed and focused. “Is there any ritual you have to do? Prayers? Yoga? Singing to Beyonce or Judy Garland?”

Jim didn’t want to ask. “I wash my face…”

They went back to Jim’s place afterward. Despite his address being on all of his information back at work, Jim was hesitant to let Michael know where he lived. He was worried Michael might start showing up at odd hours to bother him. He ushered Michael into his living room and asked him to wait while Jim got his supplies and prepped his face. Once he was finished he brought everything back and set it up on his coffee table.

Jim already planned what he wanted to do. He envisioned a demented fish creature look with dark colors and lots of prosthetics. Having already done pretty mermaids in the past, he wanted to look scarier. He started by affixing his prosthetics to make gills and ridges. Once finished with drying them, Jim began applying dark green paint as foundation before contouring and highlighting with black and forest green. From there, Jim blended the paint onto his neck and then added small details to his face like scales and guts inside the prosthetic gills. He added white contacts and painted his hands and hair. He was so invested in his makeup look that he forgot Michael was there, watching him. When Jim finally looked up, satisfied with his completed look, Michael stared back at him. He was deeply upset.

“No offense, Jimbo, but this is ugly,” Michael complained.

“No, it isn’t. My makeup is never ugly.”

“It is,” Michael insisted. “This is gross. Why would you do this? You should have done a pretty mermaid instead of a fishman nobody would ever want to fuck.”

Jim held his tongue and kept from going off on his boss. “I’ve already done traditional-looking mermaids before.”

“And those were great,” Micheal interjected.

“But I want to branch out more. I don’t wanna post the same face twice.” With that, Jim took his phone out and positioned himself for selfies. Dwight swore up and down Jim was an attention whore and only existed to be liked and admired by others. Jim hated Dwight so much that he’d argue the sky was green just to spite him. But in this case, Dwight was correct. Jim was an attention whore, and with his Instagram, he could actively court attention that he wasn’t getting in real life.

Happy with the pictures he took, Jim uploaded them to Instagram and watched as the likes poured in. Jim grinned smugly as he got platitudes for how inventive his look was and how great he was at makeup. Behind him, Michael scoffed.

“I feel cheated,” Michael grouched.

“No, don’t start this,” Jim said. “You wanted to watch _once_ and get dinner _once_. I held up my end of the bargain so I hope to never hear about this at work again.”

“I _was_ cheated! I wanted to see you do something cute and girly, and instead, I got _this_.” He gestured to Jim. “This isn’t fair! I want a redo!”

“Well, I’m not restarting. It’s already ten and I need to clean up. You should have specified what you wanted to see me do earlier.” Jim began shoving Michael out of his house, getting green and black paint all over Michael’s suit jacket. “Have a good night, Michael. I’ll see you tomorrow.” He slammed the door in Michael’s face before he could get a word in edgewise.

* * *

Jim wasn’t fortunate. He thought about his bad luck on the drive to work. He was rather unlucky in most avenues of life: career, relationships, friends, family. Bad things happened to him. So, with that in mind, Jim thought about how Michael might actively set out to ruin him over not getting the Sugar Plum Fairy makeup look he wanted. If Jim wanted to circumvent his shit luck then he needed to play into Michael’s hand.

How was this his life?

Jim got to the office early. He walked into Michael’s office with a cup of coffee and a gas station croissant sandwich. Michael was already there, scrolling through Jim’s secret Insta. 

“Good morning, Michael,” Jim said sweetly.

“What do you want, you fraud?”

Jim set the food down next to Michael’s keyboard, out of immediate reach in case Micheal’s sometimes erratic movements decided to spill coffee all over the computer motherboard (which had happened a few times). “I felt bad about yesterday. I’m sorry you were disappointed with my makeup.”

“That’s not a real apology,” Michael complained. “You’re supposed to say “I’m sorry I disappointed you.” How _disingenius_ of you.”

Well, he was right. Tricking Michael was always touch and go. “I brought you coffee?”

Michael reached over and took a sip of it. “Apology not accepted.”

“Michael, look. You’re the one blackmailing me. I shouldn’t have to apologize to you for you holding my hobbies over my head.” 

“I’m not blackmailing you, Jim. What the hell? No, we’re the only two people in on your secret! We’re protecting your secret together!”

“And then what? If I don’t do what you say you’ll stop “protecting my secret?””

Michael looked thoughtful. “I guess that’s what’s happening.”

“...so you want a redo?”

Michael nodded eagerly. “Yes! I want you to do something _pretty_ , Jim. Not beastly and ugly and like something Dwight might get off to.”

“Why does this have to be about sex?”

“It isn’t! But just be pretty, Jim. Isn’t that the point of what you do?”

Jim wanted to say no, not quite. He did it to show off his makeup skills because no one in his life either knew or cared about them. While it just so happened that Jim was good at glamorous makeup, he still liked doing horror, artsy, and camp-style makeup too. But Michael didn’t truly care about the craft or Jim wanting to explore it. He just wanted Jim to do something simple and basic, shiny enough to hold his short attention span. “Fine, come over tonight and I’ll do something cute, okay? Please don’t bother me while I’m working.”

Michael nodded happily, taking a bite out of his croissant sandwich before spitting it out due to it being too hot. Jim rolled his eyes and left Michael alone.

* * *

“Yes! This is what I wanted,” Michael cheered. He pulled his phone out and began snapping pictures of Jim’s makeup. Jim sighed and fought the urge to roll his eyes. His grandmother always told him that his eyes would get stuck if he rolled his eyes too much. Jim hadn’t believed that, but his grandmother also swore: “queers liked dresses and makeup” or something like that. So maybe she was on to something.

Jim did a fairy look, similar to something he saw on Winx Club as a kid. It wasn’t his best work by a long shot but it made Michael happy. Hopefully, this meant Jim would never have to relive this episode again. Jim went into his room to find a wig to wear for his Instagram post. He usually wasn’t a fan of wigs and didn’t wear them often but tonight seemed like a good occasion to bust one out. Maybe it’d distract from how basic his makeup was.

He came back to the living room with a long, straight, blonde wig that sported short bangs. Maybe he could add highlights to the wig using lipstick to make it stand out more…

“I bought this for you,” Michael offered, pulling a package out of a black plastic bag he brought. Jim took the package and opened it: a cotton candy pink wig. It was wavy and soft and had lace for Jim to cut. Inside the wig’s packaging were hair clips and barrettes. Jim picked out a large star and some smaller hairpins. It was a thoughtful gift Jim supposed, although he hadn’t asked for it.

“Thanks, Michael. This matches pretty well.” Jim put the wig on and started cutting the lace off.

“You’re welcome. I bought it as a gift for letting me watch last time. Thank you, kind sir. Or kind madam. Or sirdam.”

Jim rolled his eyes. “I’m finished, Michael. Is there anything else you want me to do?”

Michael shook his head and wordlessly pocketed his phone. “I’ll get out of your pink hair then.”

“Yeah.”

“See you tomorrow,” Michael asked.

Jim didn’t say anything.

“Well, I’ll show myself to the door,” Michael said awkwardly. Once he was gone Jim locked his door, making sure Michael had actually left.

He prayed that this was the end of it.

* * *

That was the end of it. At least, it was.

Michael didn’t bother him about it anymore to the point that Jim wondered if he had forgotten all about his hobby. Nobody at work made any snide comments toward him so Jim was positive that Michael managed to uphold his end of the bargain.

It wasn’t until three weeks later that Michael turned up on his doorstep.

“I want to watch,” he said by way of greeting. Jim had the mind to slam the door in his face but thought better of it. He didn’t want to go back to walking on eggshells around Michael. Instead, Jim allowed Michael in.

“You don’t get a say in what makeup I’m doing,” Jim warned. “You sit there,” Jim pointed at the couch across from where he was working, “and be quiet.”

“Can I take pictures,” Michael asked.

“Why do you need them?”

“To memorialize the moment.”

“Fine. After I post to Instagram. And I want any good pictures you take.”

Michael nodded fervently and sat down. Jim did an entire face based on Pablo Picasso before painting his neck, arms, and chest to match. He donned a wig, this time feeling it was necessary.

“I like this one. It’s artsy without being ugly, like the fishman you did that one time.”

“That fishman is one of my most liked pictures. Just because you might not appreciate what I’m trying to do doesn’t mean others don’t.”

“I never said people didn’t.”

Michael handed Jim a bag he’d been carrying. Jim initially figured it was full of snacks since Michael was the type to treat this as a tailgate. However, when he opened the bag, Jim found an expensive Michael Kors necklace inside. It had to be worth five or six hundred dollars! “Michael, I can’t take this, it’s so expensive!”

“It’s a gift, take it.”

“Michael, I can’t take something like this from you. You’re my boss, it’s inappropriate.”

“You took the wig, that cost around the same amount.”

Jim hadn’t known that when he took it. He figured that it was fifty dollars tops, like all the wigs Jim got off of Amazon or Aliexpress. He even haphazardly threw it into his closet like he did all his other wigs. Had he had known Jim would have refused that gift too. “I didn’t know. You can’t make a habit of buying me stuff.”

“Put it on,” Michael commanded. Figuring he lost this battle Jim took the necklace out of the case and put it on. While it looked nice with his makeup it blocked his neck and the work he did there. Maybe it’d look nice in future pictures…

Michael took his pictures, and after Jim deemed them to be of shit quality, left.

* * *

Michael came over a lot after that. He must have mistaken Jim not kicking him out the first time as permission to bother him, but it wasn’t. He came twice a week and would silently sit across from Jim and watch him work. Sometimes, he’d give Jim suggestions on what he wanted to see _next_ time but clearly took to heart when Jim told him he didn’t plan on entertaining his suggestions for _this_ time. Jim wished Michael listened like that at work. Once Jim was finished Michael would ask a bunch of questions about the process while making snide remarks here and there.

Sometimes, Michael would bring Jim expensive gifts. Every time he did Jim would try to refuse them. Michael would force them on Jim though, insisting that he take them “or else”. Nice dinners, jewelry, clothes, makeup, and wigs. Michael even bought him a Prada bag! Jim didn’t carry purses—he sighed just thinking about why Michael thought he’d like purses—but even he could admire the nice, trendy, costly bag. And costly it was: it retailed at fifteen-hundred dollars. Jim didn’t have to be an accountant to know Michael didn’t have that kind of money.

Jim was willing to admit to himself that he liked Michael’s attention. He liked attention in general and took it any way he could get it. Michael was more focused on him than any of his Instagram followers were, who only cared about Jim so long as he popped up on their feed. But Michael was always there, always watching him, always giving him gifts he couldn’t afford. How could Jim not like the attention?

Secretly, he found it hot.

He’d never tell Micahel that! But he did…

Jim had been single for a year since his relationship with his last boyfriend imploded. He didn’t like Jim’s job, didn’t like the fact that Jim wasn’t all that close with his family, didn’t like that Jim did makeup, and put it on Instagram. He wanted Jim to choose between the two. And at the time Jim chose Instagram—why would he give up his hobby, his fandom, and the extra income for a replaceable man? But he hadn’t been able to replace his boyfriend. He’d been a dick, sure, but he had good dick and Jim often wondered if he valued money and attention more than he did sex.

(And the answer was always yes).

Still, since Jim was super lonely he was starting to find the only in-real-life male attention he was getting to be attractive. And Michael wasn’t ugly for an old man. Once you got past his crazy eyes and oily hair he was actually kind of handsome. But it didn’t matter because Jim wasn’t so desperate that he’d try anything with Michael just because of proximity. He had morals and self-control and he would not let Michael touch him! Not that he would; Jim didn’t think Michael was interested in him. He got the sense that Michael’s weird-ass fixation on him stemmed from internalized homophobia and male attraction Michael was subconsciously trying to process and it was just luck of the draw that Jim had been the target for it instead of Oscar or even Ryan. But he didn’t harbor any feelings for Jim, not at all. Michael always referred to him as a son (or a daughter when the internalized homophobia jumped out). He probably had a crush on Ryan or the new CFO, David Wallace.

And Jim didn’t have a crush on Michael (his blackmailer!). Because that was pathetic. And Jim was not pathetic, no matter how pathetically his non-Instagram life was going.

Jim poked himself in the eye with his liquid eyeliner. He sighed; who was he kidding. He was pathetic.

* * *

Michael brought them to an expensive restaurant where their meal would cost three-hundred or something dollars. Jim was legitimately concerned about Michael’s finances. Still, he enjoyed his expensive Tex-Mex because why not? Plus, Michael put in the effort to not look messy today and Jim really appreciated that. Michael ate as silently as he could while Jim hashed out his plan for tonight’s look. “I’m thinking I want to do something grungy, kind of like Adore Delano. Do you know who that is? Of course you do, you’re obsessed with _Drag Race_. I want to look like that since I never do anything in that area. I think that black wig you gave me will look good…”

“What are you,” Michael blurted out. 

“What do you mean by “what am I”?”

Michael shrugged and looked thoughtful. Jim knew from experience that a Michael that reflected on his question before asking it was a Michael gearing up to ask a stupid question. “Are you a girl or a boy?”

“Are you asking me if I’m trans or not? No, I identify as a cis gay man.”

Michael stared at him in confusion. Jim sighed.

“I’m a boy.”

“Ah. Are you a drag queen?”

“No Michael, I’m not a drag queen. Seriously, when have you ever seen me doing drag? I’m not anything but a man who likes doing makeup. Or I suppose I’m an Instagram influencer.”

“You’re my best paper salesman.”

Jim gave Michael a tight, confused smile. The last thing Jim wanted to be known as was the best, closeted paper salesman in town. “What prompted this?”

“I’m trying to figure you out. What’s your end goal in doing this? Do you want to make a legitimate career out of this or are you content to forever hide your talents from everyone?”

That was a keen observation from Michael. Jim squinted at him. Who was _he_? Why had he replaced Michael? “I do it for fun. I didn’t expect so many people to start following me but the audience has been nice. I’m not sure if I want to make a career out of it.”

“You’d be a good drag queen,” Michael mused. “You’re funny and charming and pretty. You’d be successful doing that.”

Aw, Michael thought he was funny and charming and pretty? Jim already knew he did but it was nice to have it re-affirmed now that he had a stupid crush on Michael. “And then I’d have to leave Dunder Mifflin. Do you want that?”

“You can do both,” Michael commented before paying their bill. They went back to Jim’s place after that where Jim did his makeup while Michael watched. Today, Michael sat right beside Jim, so close that their knees touched and electrified Jim. He was blessed that Michael was so dense; the blush spreading across his face would have given his pathetic crush away to anyone else but Michael was an idiot. It made Jim all the more pathetic.

When he was finished with his makeup Jim allowed Michael to take pictures. Micahel would move his head in different directions, aware of his makeup, and doing his best not to smudge it. He recently started to pose Jim for his pictures and whenever Jim asked him why he was doing this Michael got cagey in ways so defensive that Jim couldn’t poke holes in his story. But today, the posing got weird.

Michael had Jim sit on the floor and look up at the camera while he stood over him. “Give me a sultry look.”

Jim did that.

“Now an innocent one.”

Jim did that too. “Why am I doing this?”

“So I can document your face.”

“I already do that,” Jim complained. He stood up and reached for Michael’s phone. “That’s literally the whole point of Instagram.”

“Just shut up and let me do this.”

Michael accidentally elbowed Jim the stomach trying to keep his phone away from him. Jim momentarily had the wind knocked out of him and felt himself drool at the sudden impact. Michael firmly grabbed Jim’s jaw and held it, watching as the saliva slowly rolled down Jim’s chin. He held it tightly and forced Jim to sit back on the floor. Once Jim was back into position Michael snapped a final picture.

“You should clean that up,” Michael said, voice high and tight.

Jim nodded in confusion. Michael practically ran out of Jim’s house after that, leaving Jim on the floor, wondering if his spit somehow set Michael off.

* * *

Micahel didn’t come over for a while after that. Jim was glad. He was no longer being blackmailed and didn’t have to give up his evenings to entertain his childish boss. No more gifts that Jim felt bad about taking. No more crushes on Michael fucking Scott. Now, Jim could do his makeup in peace. What could be better?

It was kind of boring doing it to an audience of no one. Jim thought about inviting his friends over to help him along or going on Instagram Live while he did it but it wasn’t the same. He did some of the rather basic ideas Michael gave him and found himself angry when Michael didn’t like his pictures. Michael also ignored him at work and was uncharacteristically quiet during the day. Everyone enjoyed his silence, including Dwight, but Jim knew there was something up. And it all had to do with his drool.

After a month of radio silence, Jim decided to confront Michael. He knocked loudly on Michael’s office door and when Michael ignored him, he barged in. “Michael, let’s go to lunch.”

“Sorry Jimbo, but I have a lot of work to do, a lot of calls to take…”

“Cut the shit, Michael! Pam said your schedule is empty today. We’re going to lunch and you’re paying!”

Jim stood outside and waited for Michael to come. He led them to Chipotle—just because he was mad at Michael didn’t mean he’d make his pockets bleed (any more than he had over the last few months)—and waited for Michael to pay for their food.

“I shouldn’t have to pay for your lunch,” Michael grouched.

“Whatever, you’ve been doing for months. I don’t know why you're complaining now.”

They sat across from each other and stared awkwardly at one another. “Jimbotron, what can I do for you?”

“Why are you avoiding me,” Jim asked. “Did I do something to you? This cannot be because _you_ elbowed _me_ and then took pictures of it? What gives?”

“I’ve decided that blackmailing you is no longer fun. I have better things to do.”

“Like what?” 

“Erm. Well…”

“Fine, Michael! But give me your phone. You can’t keep any of the pictures you took of me. I don’t trust you to not show them to anyone.”

Michael looked distraught at that and tightly gripped his phone. Jim had to wrestle the phone away from Michael. Jim paused at Michael’s lock screen photo: it was a picture of Jim in makeup. It was one of his more glamorous looks with a long, curly, sandy blonde wig, jeweled earrings Michael got him, and a dress. His Instagram followers would obviously know he was a man and Michael obviously knew since Jim didn’t identify as anything else but anyone not in the know would think he was a woman because he looked like it.

Was Michael trying to pass him off as his “girlfriend”?

“Michael, what the hell? Is this why you’ve been taking pictures of me?”

Michael started fidgeting the way he did when he was caught in a lie. His eyes looked everywhere but at Jim’s face. Jim should have been annoyed that Michael wasted his time for _months_ just to snap pictures of him to show off to his family. Wouldn’t it have been easier to get a real girlfriend? What was even the purpose? Jim really should have been annoyed that Michael was using him as a catfish!

But at the same time, he was flattered.

Did this mean Michael liked him back?

“What does any of this mean, Michael? Have you been showing people pictures of me, trying to pass me off as your partner?”

“I could show you better than I could explain…”

Jim sat back in his chair and waited for Michael’s half-baked explanation. 

“Tomorrow, I’ll show you,” Michael clarified. “But I need you to do something for me too.”

Jim leaves in at that, intrigued. “What do you need me to do?”

“Well…”

* * *

Jim did what Michael asked of him. He had strange three requests of Jim: wear falsies, the kind that was the color of Jim’s actual eyelashes. He asked that Jim wear clear lip gloss. Specifically lipgloss and that he’d be able to tell if Jim wore chapstick instead. He wanted Jim to style his hair differently. Michael showed him a few styles he liked. While short, they were androgynous, bordering on feminine hairstyles. He wanted Jim to look as femme as he could possibly look without tipping off others to what he was doing.

This was a dangerous game they were playing but the thing with Michael was he might have not realized that. Or maybe he did and that was the point. The thought of coming to the office in makeup terrified Jim but also stirred something deep within the pit of him that he didn’t want to acknowledge. He didn’t want to acknowledge how it was an extension of the swirling feelings Michael Scott had caused him for the past few months.

“Nice haircut,” Pam said when she saw him.

Jim gave her a tight smile. “Thanks, thought I’d try something new.”

“What have you done to your face,” Dwight questioned. He got close to Jim’s face, noses touching and stared deep into Jim’s eyes. Dwight was so close that Jim was sure he’d see where the fake lashes were attached but instead Dwight pulled back, mumbling under his breath about pranks and Jim needing to be fired. That continued for the rest of the day, Dwight fixating on Jim’s appearance and coming _so_ close to realizing Jim had on makeup but failing to draw that specific conclusion. He was peeved and uncomfortable and Jim had to admit that this was better than any prank he could have pulled, especially since no one else noticed anything amiss with his appearance. Maybe he’d do this again if only to fuck with Dwight.

Michael hadn’t interacted with him all day.

Jim was perplexed. Hadn’t he done what Michael wanted?

Jim lingered after work, watching as everyone filed out of the office. Everyone except Michael. Jim wanted to catch him before he left and ask him what the point of this thing was. When Jim stood to enter Michael’s office to ask him about it, he was stopped by Michael’s voice.

“I need you on the phone, Ms. Halpert, lest you miss putting one of my clients through to me.”

Befuddled, Jim asked, “what?”

“Ever the bimbo, are you. I don’t pay you to stand around with your mouth open. Get back to work.”

Jim felt a lot of things at that moment. Anger, hurt, betrayal, disgust. But mostly, he felt hot. Like lava was settling in his stomach and spreading through his veins. Jim knew what he was feeling but chose not to put words to it. Instead, he walked back to his desk and sat down. 

He could feel Michael glaring at the back of his head. Realizing his error, Jim moved to the reception area. The moment he sat down, Jim received a call. He answered it.

“ _I’m expecting a few calls this evening. For the next forty-five minutes, you are to answer the phones, give your name, and transfer them through to me. If you make a mistake you can expect to be punished. Are we clear Ms. Halpert?_ ”

Jim looked at Michael through the blinds. He gave him a small nod.

“ _Answer me, Ms. Halpert._ ”

“Yes, sir.”

“ _Good girl._ ”

That went straight to Jim’s crotch. He had to fold his legs at his thighs to control the tightness pooling in his work slacks. Trying to keep his breathing in check, Jim stared at the phone and tried figuring out how to transfer Michael’s calls to him. Just as Jim began to get comfortable with the phone, someone called Dunder Mifflin.

“Dunder Mifflin, Ms. Halpert speaking.”

The voice on the other line laughed. “ _Ms. Halpert, huh. What happened to the old receptionist, Pam?_ ”

“She’s taking time off,” Jim stuttered out. Jim wasn’t stupid and knew the other person on the line was Michael calling from his cell phone. Still, Michael was taking this far and Jim wanted to see how long this would continue. “How may I transfer your call?”

“ _Now hold on sweet thing, I’m not finished with you yet._ ”

Jim was so hot. So, so, so hot. “Oh?”

“ _What a beautifully distracting voice you have. It sounds so lewd and sexual. I’m sure you’ve heard that before, right sweetheart?_ ”

“No, not at all…”

“ _Really? None of your boyfriends have told you how sexy you sound? I can only imagine how nasty you sound while being fucked in your sopping pussy like the slut you are._ ”

Whoa. Jim never imagined Michael to have a dirty mouth. But he never thought about it, not really. Now here Jim sat, painfully hard from Michael Scott whispering filthy words in his ear. Jim tried saying something in response but a needy whine escaped his throat instead.

“ _You like that, huh? Slut._ ”

Jim nodded. 

“ _This is probably how every evening starts for you. Letting some stranger talk dirty in your ear while you try your hardest not to finger your cunt right where you stand? Am I correct? Or do you not stand? Do you push your panties aside and get on your knees before rubbing your clit? I bet you put on quite the show for those around. I’m just imagining it: you on your knees in the middle of the street or the grocery store, or maybe the warehouse at Dunder Mifflin. You’ve pulled your frilly, pink panties down to your ankles. I’d imagine you rubbing your pink, swollen clit with one hand while holding your phone with your other hand. Or, better yet, I bet it’s the warehouse workers whispering to you. Touching yourself while they talk dirty to you. Spreading your juices everywhere. I bet you’d leak everywhere, you’d be so wet. Making the floor around you slick. You’d slowly start to finger your wet, loose, pussy in front of the entire warehouse. Your long fingers wouldn’t be enough though, you could stick your whole fist in your cunt and it wouldn’t be enough. You’d be begging someone to come and fuck you, anyone. Maybe everyone. One of the warehousemen would lay you on your back, on top of your mess, and take you right in front of all your coworkers. And like the little whore you are, you’d love it. I’d bet he’d fuck you so hard you’d be out of your mind with lust, moaning. They’d have to shut you up by stuffing your mouth full of cock. They’d take turns fucking your slutty mouth and your abused pussy until your cunt was so sore you could no longer feel cocks entering you. Only after everyone’s cum would you be allowed to leave and on your drive home, you’d be rubbing yourself, thinking of how you’d do the same tomorrow._ ”

Wow. Jim tried his hardest not to start touching himself, but he couldn’t help it. He began palming himself through his slacks, humping his hand while Michael degraded him. At the visual image of himself being pushed down and taken by his coworkers like an animal in heat, Jim stuck his hand into his pants. He slowly stroked himself but was unsuccessful in pumping his fist due to how tight his slacks were. He removed his hand to unbutton his slack and squatted to shimmy out of them without alerting Michael to what he was doing. Once free, Jim began to stroke himself with abandon. He kicked his pants and underwear off, getting them tangled on his shoes. He tried to maintain eye contact with Michael through the blinds but found himself throwing his head back and closing his eyes. He panted out as Michael outlined his fantasy, probably alerting him to how hot and bothered it made Jim.

A hand slammed down on the reception desk causing Jim to drop the phone. He quickly attempted to stuff himself back into his underwear only to realize they were pooling around his ankles, leaving him exposed.

Michael looked down at him with both barely concealed fury and levity. “I thought I told you to transfer my calls to me. Instead, you’re getting off to the voice of some random office drone trying to place an order. Are you such a dickpig that even an ugly male voice turns you on? Such a cum dumpster that you couldn’t make it home, if not the restroom before you fingered yourself? You want to be used that badly, Ms. Halpert?”

Jim shuddered. Despite no longer touching himself, hearing Michael call him such foul names caused Jim to unload all over Pam’s workstation. Embarrassed, Jim reached for tissues to wipe away his cum with. Michael grabbed his hand and held it tightly.

“A dirty slut like you should clean it with her tongue, don’t you think?” Michael moved around the reception area and gripped the back of Jim’s neck, forcing his face into his mess. He smeared Jim’s face in it, getting cum in his hair and eyelashes. Jim tried to complete the task asked of him and stuck his tongue out to collect some of his cum. Michael saw Jim eating his jizz and stood back to watch the sight in front of him. He slapped Jim’s bare ass and said, “clean the entire workstation while you’re at it. We wouldn’t want Pam to wonder why certain parts of her desk were clean and others weren’t, would we?”

Jim could feel himself growing hard again. He licked Pam’s keyboard and mouse, before moving to the desk around it. Along with his cum, Jim licked up dust, small bits of paper, and maybe even one of Pam’s nail clippings. Not confident in himself to determine when Michael wanted him to stop, Jim continued to lick over spots he had already “cleaned” (and made a mental note to wipe Pam’s area down with Lysol wipes once everything was said and done). He continued until Michael slapped his ass again, hitting the area between his hole and his heavy balls. He turned around to look at Michael, face crusted with cum and eyes laced with desire.

Michael regarded him with disgust. “I just lost a very important client due to your slutty hole. Do you realize that you dumb bimbo slut? You need to be punished. You have five seconds to get into my office.” 

Jim scrambled to get into Michael’s office but tripped. He heard Michael laugh.

“Since you’re down there, you can crawl into my office like the pig you are.”

Jim did as he was told. He sat in the middle of Michael’s office on his knees, just like in Michael’s fantasy. And like in said fantasy, Jim was aching with need. Michael stepped into the office after Jim, closing the blinds as he went. He stood behind Jim and tapped his foot. Jim craned his head back to stare at Michael.

“Strip,” Michael commanded.

Jim wasted no time unbuttoning his shirt before folding it. He then kicked off his shoes before pulling his slacks and underwear off in one fell swoop. His cock was on full display, angry and red, and at full-mast. Michael circled Jim before standing right in front of him. He tsked when he saw Jim’s weeping, swollen cock.

“How tiny,” Michael commented. He reached down and tugged on Jim’s cock. It _was_ small, especially compared to the rest of Jim’s frame. It was barely four inches flaccid although it managed to look bigger once erect. Not that it mattered. Jim had a clear preference for bottoming so whether or not his dick was big for utility’s sake wasn’t important. Michael tugged on it again.

“Ahh,” Jim moaned out.

“A pretty little bitch like you has a pretty little pussy to match. I’m not shocked.” Michael reached into his pocket and pulled out a cock ring. Jim groaned at the sight of it, dreading how the tight-fitting item would impede his impending orgasm. Michael slipped it on Jim’s cock and admired his handiwork. Then, he sat down at his desk.

Confused, Jim watched Michael’s actions. He seemed to be working although Jim couldn’t imagine Michael working when he could be fucking; he couldn’t imagine Michael working when Michael was supposed to be working.

“Michael—,”

Michael gave Jim a smoldering glare. “You are not to call me by my first name. In front of your coworkers, you are to call me Mr. Scott. In private, you are to call me Daddy. Do I make myself clear?”

“Yes.”

“Yes what, bitch?”

“Yes, daddy.”

“Come here.”

Jim stood to move around Mich— _Daddy’s_ desk but thought better of himself. Instead, he crawled around his Daddy’s desk and sat beside his feet.

“Get under the desk,” Michael sat without looking up from his computer. Jim fitted his long body underneath Michael’s desk and waited for further instruction. “Open my pants and take my cock out,” Michael said, “I want you to warm my cock for me. Try to fight your natural urges to suck on it and hold it in your mouth while I work.”

Jim fumbled to unbuckle Michael’s belt before finally getting it free. Despite the lack of light underneath the desk, Jim could tell Michael was big. Like super big. He took the tip of Michael’s cock into his mouth and savored the taste of the precum on the head. Jim had never been a fan of the taste of semen but it had been so long since he last had sex that he welcomed the taste like an old friend. He slowly took Michael into his throat, careful not to swallow him down lest he’s accused of sucking his daddy off. When Jim took Michael as far as he could go he paused. His nose was nestled in Michael’s pubes, the strong scent of musk and sweat wavering off of them. The smell assaulted Jim’s senses and made him even harder. His poor cock strained against his cock ring causing Jim to moan out, the vibrations of which massaged Michael’s cock.

“You really can’t help yourself,” Michael marveled. “You’re a natural-born dickpig. You obviously love being fucked too much to be of use elsewhere. I can’t believe I caught you masturbating on the job. I should fire you and lock you away in my bedroom. Keep you plugged and stuffed with toys until I get home to fuck you. Maybe I’ll rent you out so you can earn your keep. That’s what you want, isn’t it? You practically prostitute yourself on Instagram, you might as well get a pussy railing out of it. Or would you prefer it if I kept you here and allowed you to service the men of the office? I’m sure you’d like that, being filled at every waking moment, existing as nothing more than an incentive for the big, burly men of the office. Maybe I’d take out the urinal in the bathroom and have you sit there all day, naked and waiting to be drenched in piss.”

Seriously, where did Michael learn to talk like that? Jim didn’t even care anymore, it was so hot. He never thought he’d be into degradation like this yet here he kneeled, a flaccid cock in his mouth, his cock caged, and his mind honestly debating the pros and cons of being a human urinal.

Michael sat quietly and typed away at his computer, genuinely working. Every now and again, Michael would shift in his seat, dragging his cock across Jim’s prone tongue. Sometimes, he’d thrust his cock deeper into Jim’s mouth, hoping to gag him. He’d be disappointed to find out Jim had no gag reflex; it was the first time ever that Jim was sad that he didn’t.

After what had to be an hour, Michael pulled his cock out of Jim’s mouth. While feeling empty, Jim’s jaw and knees were happy for the break. Michael grabbed a fistful of Jim’s hair and he got the hint to come from under the desk unless he wanted Michael to pull his hair out.

“I managed to email those clients I was waiting on a phone call from and discuss business with them. But don’t think I’ve forgotten your punishment, slut. Stand in front of my desk.” 

Jim crawled back over to the front of Michael’s desk. He sensed that crawling around would be his new normal so long as he continued to allow Michael to play with him. He stood and faced the window overlooking the parking lot, anticipating what would come next. 

“Hands on the desk, ass out.”

Jim got himself into position. He felt a hard blow come down on his ass which nearly knocked him into Michael’s computer monitor. He forced himself back up on his hands only for another blow to knock him back over. Jim quickly peered behind him and saw Michael holding his belt in one hand. He brought it down again, this time nicking Jim’s hole with the belt.

“Ahhh,” Jim cried out. Michael hit him harder at the sound.

“Be quiet, bitch. You wouldn’t want Hank and the cleaning staff to hear you.”

With each blow, Jim found it harder and harder to be silent. By the end of it, he was a moaning, whimpering mess, lost in a lusty haze. His mind couldn’t focus on anything other than being his daddy’s bitch and getting his pussy fucked. His thoughts were so consumed with being Michael’s forever-bitch that he hadn’t noticed his daddy adding nipple clamps to his chest. Jim howled in pain-driven pleasure. So horny he was that he could barely stop himself from licking his fingers and inserting one into his red, puffy hole. He braced himself against Michael’s desk and finger fucked himself open, not caring if doing so would bring him further punishment.

Jim heard the sound of something metal hitting the ground before cool hands spread his cheeks open, giving him better leverage to fuck himself. Quickly as the hands came they left. “Ahhh,” Jim moaned at the loss of the cool contact on his burning ass. Soon, they were back with something chill dripping down onto his hole. Recognizing it as lube, Jim removed his finger from his hole and coated his remaining fingers in it. Then, he stuck two fingers into his opening and began scissoring himself.

“There’s no point in me penalizing you for doing what you were born to do,” Michael said, amusement clear in his voice. “You’re just so greedy. You don’t care about satisfying your daddy, do you?”

“Yessss, I doooo,” Jim cried, thrusting harder inside himself. 

“You’re a selfish little girl, that’s what you are. If you cared about my pleasure you would have waited for me to use you and come before you focused on your own needs. But you’re a bitch in heat and just want to rut against something. I could find a homeless man right off the streets right now and you’d let him fuck your loose pussy, wouldn’t you.”

“Ahh, yesss,” Jim whined. “I need to be fucked, daddy!”

“I know you do baby, and that’s why I’m not punishing you. Maybe next time I’ll take you down to skid row and let all the bums use you. But first, I have to break you in myself.”

Jim could hear Michael pushing his pants down before he pulled Jim’s fingers from his leaking hole. Jim whined at the loss. He pushed back, trying to hump Michael’s leg instead but found himself rutting his bound and hard cock on Michael’s desk instead. His daddy was generous enough to spread his legs using his thigh, giving Jim something concrete to hump himself against.

“Ahh, ahh, ahh,” Jim moaned, feeling the orgasm he couldn’t have building up. “Daddy, please—!”  
  


Michael pressed his clothed crotch against Jim’s drenched hole started rutting himself against Jim’s ass. “You need to beg better than that unless you want me to cum without ever entering you.”

Jim needed to cum, needed Michael to cum in him. “Please daddy, fuck me! Fuck me, please!”

“I guess I’ll cum on this fine ass of yours before handcuffing you and leaving you for the cleaners to find. I believe there were a few men on the staff who’d find your abused cunt appealing. Otherwise, you’d be waiting until Monday when the cameramen get here. Maybe they’d use you, maybe they’d film you. Who knows?”

Jim didn’t want to spend the whole weekend hard, waiting to be fucked, waiting to cum. He needed to beg better. “Please daddy, I need you to fuck me, need you to use. Just you, only you. I want you to fuck my slutty pussy. Please?”

Michael leaned over and kissed Jim on the back of the neck. “You’re such a spoiled brat, you know that? You can’t even beg properly, probably because you’re used to everyone giving you everything with minimal effort. Me too; I’ll give you anything you want. So if you want me to fuck you, then…”

Jim felt something prodding at his opening before pushing in. He gripped the edge of Michael’s desk as hard as he could as his boss-turned-daddy entered him. Michael grabbed one of his shoulders and wrapped his free arm around Jim’s waist to better leverage himself. He began thrusting shallowly, and Jim thought it was for his own benefit rather than getting Jim off. He deserved that after fingering himself with no care for Michael. Slowly but surely, Michael began to pick up his pace and the depth of his strokes. Soon, he was rapidly pounding into Jim, holding onto him by both of his shoulders. Michael bit him hard on the shoulder, and then his shoulder blade while licking and kissing down his spine.

Then Michael pulled out. He walked over to his small couch and sat down. He folded his arms behind his head and watched Jim. “I'm tired of giving you my all while getting nothing in return. If you want to get off then you’ll ride me.”

Jim scrambled over to Michael and sat on his cock in one fell swoop. Michael rewarded him by taking the cockring off. Jim lifted himself off of Michael’s lap before quickly lowering himself down. He bounced on Michael trying to chase his impending orgasm. Not wanting to leave Michael out Jim clenched his ass as tight as he could while he moved. Michael responded by digging his nails into Jim’s hips.

“I’m going to cum,” Michael said. “I expect you to take all of it and leave it in your pussy on your way home. Understood?”

Jim nodded. “Yes, daddy,” he moaned out.

With that, Michael exploded into Jim. Jim followed him by cumming all over the front of Michael's shirt. Jim raised himself off of Michael's flaccid cock and clenched his ass so no cum would come out.

“I have a plug in the top left drawer of my desk. Use that.”

Jim found the plug and inserted it into himself without dropping any of Michael's cum.

Jim re-joined Michael on the couch, collapsing on Michael’s lap. He felt tired, his knees hurt, and he felt dirty all over (he _really_ needed to clean Pam’s desk). But he was also thoroughly satisfied. Jim would have taken any kind of lay at this point in his life, he was so lonely and horny, but he never expected Michael would be so kinky and domineering! He wondered where Michael even learned this and asked him.

“Porn,” Michael said jovially, dropping the daddy act and reclining on the couch. “Was I any good?”

Jim rolled his eyes and carded his hand into Michael’s hair. He rubbed Michael’s scalp and watched as Michael melted onto his shoulder. “I should have known. What would you have done if I rejected your advances? You should have discussed this with me before going E. Edward Grey on me.”

“You’re so tightly wound and stuck up that I thought you needed a good fuck to loosen up so I gave it to you.”

Jim ignored Michael’s jab. “And who told you that that was the best way to loosen someone up? Porn?”

“Packer!”

Jim rolled his eyes again. “You still need to explain yourself to me, Michael. The blackmail, the pictures, this stunt.”

“I’m attracted to you,” Michael said, sighing. “I always thought you were an attractive male specimen but ignored those feelings. It wasn’t very manly of me to like another man, no offense to you Jim since you like men exclusively. But at the same time, you’re not manly at all, you’re practically a girl.”

“I’m not a girl,” Jim interrupted. Michael ignored him. 

“Then I found your Instagram. I was so confused. You were a girl on Instagram and a boy in person—”  
  


Jim rolled his eyes for the umpteenth time. “I’m not a girl, ever!”

“Shut up. Don’t interrupt me, please. I was confused because I found you attractive as a girl. I thought maybe you were a girl and then it would be okay that I thought you were cute during the day. Like you were hiding. But you’d come to work and you’d be a guy again and I didn’t know what to do. Then I thought maybe you were a trann—”

Jim gave Michael a tense, pointed look telling him not to proceed with his slur.

“—a boy who wanted to be a girl. And if you thought you were a girl then I’d agree with it and it’d be okay I liked you because you were a girl! But you weren’t a girl. You weren’t a drag queen either. Just a man who was good at makeup. And I had to learn that I was attracted to you even though you were a man.”

So Jim had been right about Michael unpacking his homophobia and coming to terms with being not-straight via him. “But that doesn’t explain the pictures.”

Michael looked guilty like a child who was caught stealing from the cookie jar. “I used them to masturbate.”

Jim had no words for that.

“I want to be your sugar daddy,” Michael continued. “We can date and in exchange, I’ll buy you things and give you money. You like that arrangement, right? All you have to do is be cute, makeup, or no makeup, and I’ll take care of the rest.”

Jim made more money than Michael did just as a salesman. Then, when he factored in the endorsements and ads he did on Instagram, Jim had to be making one-point-five times as much as him. He couldn’t in good faith continue to take gifts from Michael that he couldn’t afford. Still, against his better judgment, Jim did want to try dating Michael. He was attracted to Michael and the foreplay and sex was mind-blowingly great. Maybe he could teach Michael how to be a normal human being too. Plus, Jim always wanted to be a being a sugar baby to an older man. One who actually had money, sure, but being one to Michael in name only would be fun.

“Sure, we can date. We just need to keep it quiet. We wouldn’t want Toby blowing a gasket would we?”

Michael frowned at Toby’s name. “We wouldn’t.”

Jim smiled before kissing Michael on the mouth, all tongues. 

Being blackmailed wasn’t that bad.

Maybe secrets were a good thing.

**Author's Note:**

> I'm sorry I wrote this. I had this dream (twice!) and needed to write it. Or maybe it should have stayed in the drafts.


End file.
